JP2013538235A5 - - Google Patents
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- Publication number
- JP2013538235A5 JP2013538235A5 JP2013529408A JP2013529408A JP2013538235A5 JP 2013538235 A5 JP2013538235 A5 JP 2013538235A5 JP 2013529408 A JP2013529408 A JP 2013529408A JP 2013529408 A JP2013529408 A JP 2013529408A JP 2013538235 A5 JP2013538235 A5 JP 2013538235A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- cycloalkenyl
- cycloalkyl
- alkyl
- alkenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 substituted Chemical class 0.000 claims 164
- 125000000753 cycloalkyl group Chemical group 0.000 claims 69
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 64
- 125000005842 heteroatoms Chemical group 0.000 claims 64
- 229910052717 sulfur Inorganic materials 0.000 claims 64
- 125000000217 alkyl group Chemical group 0.000 claims 61
- 229910052757 nitrogen Inorganic materials 0.000 claims 58
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 55
- 125000001072 heteroaryl group Chemical group 0.000 claims 54
- 229910052760 oxygen Inorganic materials 0.000 claims 44
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 29
- 125000003107 substituted aryl group Chemical group 0.000 claims 27
- 125000000304 alkynyl group Chemical group 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 8
- 230000002401 inhibitory effect Effects 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
- 125000004450 alkenylene group Chemical group 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000004419 alkynylene group Chemical group 0.000 claims 6
- 229910052805 deuterium Inorganic materials 0.000 claims 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 5
- 239000003937 drug carrier Substances 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 239000000546 pharmaceutic aid Substances 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 229940002612 prodrugs Drugs 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011780 sodium chloride Substances 0.000 claims 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 241000711549 Hepacivirus C Species 0.000 claims 3
- 241000700605 Viruses Species 0.000 claims 3
- 230000000208 anti-hepatitis Effects 0.000 claims 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 101710036216 ATEG_03556 Proteins 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 101710003000 ORF1/ORF2 Proteins 0.000 claims 2
- 101700030467 Pol Proteins 0.000 claims 2
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 2
- 229960000329 Ribavirin Drugs 0.000 claims 2
- 206010047461 Viral infection Diseases 0.000 claims 2
- 208000001756 Virus Disease Diseases 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 101710004466 rgy Proteins 0.000 claims 2
- 101710030364 rgy1 Proteins 0.000 claims 2
- 101710030359 rgy2 Proteins 0.000 claims 2
- 230000017613 viral reproduction Effects 0.000 claims 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N Amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
- 229960003805 Amantadine Drugs 0.000 claims 1
- 102000005741 Metalloproteases Human genes 0.000 claims 1
- 108010006035 Metalloproteases Proteins 0.000 claims 1
- 229910001573 adamantine Inorganic materials 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000003429 antifungal agent Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 108010032844 hepatitis C virus NS3 protein Proteins 0.000 claims 1
- 230000000051 modifying Effects 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 0 C*(C*(C)IC(C(OC(*)(CC1C(NC2(C(*)C2)C(*)=O)=O)CN1C(C(*)N*N=C)=O)=NC(*)=C(C)*)=*)*C(C=C*)=C Chemical compound C*(C*(C)IC(C(OC(*)(CC1C(NC2(C(*)C2)C(*)=O)=O)CN1C(C(*)N*N=C)=O)=NC(*)=C(C)*)=*)*C(C=C*)=C 0.000 description 7
- UAEPNZWRGJTJPN-UHFFFAOYSA-N CC1CCCCC1 Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- OVRKATYHWPCGPZ-UHFFFAOYSA-N CC1CCOCC1 Chemical compound CC1CCOCC1 OVRKATYHWPCGPZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38505810P | 2010-09-21 | 2010-09-21 | |
| US61/385,058 | 2010-09-21 | ||
| US201161499994P | 2011-06-22 | 2011-06-22 | |
| US61/499,994 | 2011-06-22 | ||
| US201161504616P | 2011-07-05 | 2011-07-05 | |
| US61/504,616 | 2011-07-05 | ||
| PCT/US2011/052304 WO2012040167A1 (en) | 2010-09-21 | 2011-09-20 | Macrocyclic proline derived hcv serine protease inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015241811A Division JP6352238B2 (ja) | 2010-09-21 | 2015-12-11 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013538235A JP2013538235A (ja) | 2013-10-10 |
| JP2013538235A5 true JP2013538235A5 (ru) | 2014-04-10 |
| JP5857053B2 JP5857053B2 (ja) | 2016-02-10 |
Family
ID=45817947
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013529408A Active JP5857053B2 (ja) | 2010-09-21 | 2011-09-20 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2015241811A Active JP6352238B2 (ja) | 2010-09-21 | 2015-12-11 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2018107455A Active JP6574023B2 (ja) | 2010-09-21 | 2018-06-05 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2019148420A Pending JP2020015730A (ja) | 2010-09-21 | 2019-08-13 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2021004680A Ceased JP2021063130A (ja) | 2010-09-21 | 2021-01-15 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015241811A Active JP6352238B2 (ja) | 2010-09-21 | 2015-12-11 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2018107455A Active JP6574023B2 (ja) | 2010-09-21 | 2018-06-05 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2019148420A Pending JP2020015730A (ja) | 2010-09-21 | 2019-08-13 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
| JP2021004680A Ceased JP2021063130A (ja) | 2010-09-21 | 2021-01-15 | 大環式プロリン由来ｈｃｖセリンプロテアーゼ阻害剤 |
Country Status (42)
Families Citing this family (48)
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| TW201119667A (en) * | 2009-10-19 | 2011-06-16 | Enanta Pharm Inc | Bismacrocyclic compounds as hepatitis C virus inhibitors |
| UA116616C2 (uk) | 2010-09-21 | 2018-04-25 | Енанта Фармасьютікалз, Інк. | Інгібітори hcv серинової протеази, отримані з макроциклічного проліну |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| EA025560B1 (ru) | 2012-10-19 | 2017-01-30 | Бристол-Майерс Сквибб Компани | Ингибиторы вируса гепатита с |
| EP2914598B1 (en) | 2012-11-02 | 2017-10-18 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2014070964A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9409943B2 (en) | 2012-11-05 | 2016-08-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2964664B1 (en) | 2013-03-07 | 2017-01-11 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US10286029B2 (en) * | 2013-03-14 | 2019-05-14 | Abbvie Inc. | Method for treating HCV |
| US20180042982A1 (en) * | 2013-03-14 | 2018-02-15 | Abbvie Inc. | Methods for Treating HCV |
| US20140275099A1 (en) * | 2013-03-14 | 2014-09-18 | Abbvie Inc. | Methods for treating hcv |
| CN106456621A (zh) * | 2013-03-14 | 2017-02-22 | 艾伯维公司 | 用于治疗hcv的方法 |
| PL2968302T4 (pl) * | 2013-03-14 | 2018-04-30 | Abbvie Inc. | Kombinacja bezpośrednio działających środków przeciwwirusowych i rybawiryny do leczenia pacjentów z HCV |
| US20200368229A9 (en) * | 2013-03-14 | 2020-11-26 | Abbvie Inc. | Methods for Treating HCV |
| US11484534B2 (en) * | 2013-03-14 | 2022-11-01 | Abbvie Inc. | Methods for treating HCV |
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| CN105658219A (zh) * | 2013-10-25 | 2016-06-08 | 艾伯维公司 | 用于治疗hcv的方法 |
| ES2724460T3 (es) | 2013-12-23 | 2019-09-11 | Gilead Pharmasset Llc | Síntesis de un tripéptido que inhíbe el NS3 del virus de VHC macrocíclico |
| ES2708993T3 (es) * | 2013-12-23 | 2019-04-12 | Gilead Sciences Inc | Formas cristalinas de un tripéptido macrocíclico inhibidor de NS3 del VHC |
| EP2899207A1 (en) | 2014-01-28 | 2015-07-29 | Amikana.Biologics | New method for testing HCV protease inhibition |
| US9321807B2 (en) | 2014-06-06 | 2016-04-26 | Abbvie Inc. | Crystal forms |
| TWI721947B (zh) | 2014-06-11 | 2021-03-21 | 美商基利法瑪席特有限責任公司 | 抗病毒化合物的固態形式 |
| US9809576B1 (en) * | 2014-07-18 | 2017-11-07 | Abbvie Inc. | Synthetic route to anti-viral agents |
| US9809534B1 (en) | 2014-07-21 | 2017-11-07 | Abbvie Inc. | Difluoroalkylcyclopropyl amino acids and esters, and syntheses thereof |
| US10059969B1 (en) | 2014-10-03 | 2018-08-28 | Abbvie Inc. | Process for the preparation of (S)-2-amino-non-8-enoic acid |
| US10316338B1 (en) | 2015-01-30 | 2019-06-11 | Abb Vie Inc. | Enzymatic process for the preparation of (1S,2R)-2-(difluoromethyl)-1-(propoxycarbonyl)cyclopropanecarboxylic acid |
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| US20160375017A1 (en) | 2015-06-26 | 2016-12-29 | Abbvie Inc. | Solid Pharmaceutical Compositions for Treating HCV |
| AU2016283018C1 (en) | 2015-06-26 | 2022-03-03 | Abbvie Inc. | Solid pharmaceutical compositions for treating HCV |
| CN107921038A (zh) | 2015-07-08 | 2018-04-17 | 艾伯维公司 | 用于治疗hcv 的方法 |
| CA2992722C (en) | 2015-07-17 | 2023-10-17 | Abbvie Inc. | Solid pharmaceutical compositions for treating hcv |
| KR101726567B1 (ko) | 2016-07-08 | 2017-04-13 | 박공영 | 수직형 식물 재배장치 |
| AU2018215337A1 (en) | 2017-02-01 | 2019-08-22 | Abbvie Inc. | Enzymatic processes for the preparation of (±)-2-(difluoromethyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acid and(±)-2-(vinyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acid |
| CA2994496A1 (en) | 2017-02-14 | 2018-08-14 | Abbvie Inc. | Methods for treating hcv |
| CA2981993A1 (en) * | 2017-08-02 | 2019-02-02 | Abbvie Inc. | Methods for treating hcv |
| WO2019046569A1 (en) * | 2017-09-01 | 2019-03-07 | Abbvie Inc. | METHODS FOR THE TREATMENT OF HCV |
| WO2019074507A1 (en) | 2017-10-12 | 2019-04-18 | Abbvie Inc. | METHODS FOR THE TREATMENT OF HCV |
| CN107739319A (zh) * | 2017-10-31 | 2018-02-27 | 上海同昌生物医药科技有限公司 | 一种Glecaprevir合成中间体及其胺盐的制备方法 |
| WO2019084740A1 (zh) * | 2017-10-31 | 2019-05-09 | 上海同昌生物医药科技有限公司 | 一种Glecaprevir合成中间体及其胺盐的制备方法 |
| CN108329332A (zh) * | 2018-03-16 | 2018-07-27 | 安徽华昌高科药业有限公司 | 一种制备Glecaprevir的方法 |
| EP3952838A1 (en) | 2019-04-08 | 2022-02-16 | Abbvie Inc. | Solid pharmaceutical compositions for treating hcv |
| US11100900B2 (en) | 2019-06-12 | 2021-08-24 | Lg Display Co., Ltd. | Foldable display and driving method thereof |
| WO2021137256A1 (en) | 2020-01-03 | 2021-07-08 | Mylan Laboratories Limited | Polymorphic forms of glecaprevir |
| WO2021209563A1 (en) | 2020-04-16 | 2021-10-21 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| CN114085458A (zh) * | 2021-12-08 | 2022-02-25 | 宁波塑之华塑化有限公司 | 一种高强度高韧性阻燃聚丙烯复合材料及其制备方法 |
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